What are the top rated Cottage Rentals in Windsor and Maidenhead?

There are a lot of options in Windsor and Maidenhead. If you plan on staying in the Windsor and Maidenhead area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windsor and Maidenhead: <a href="/property/beautiful-windsor-cottage-amazing-location-the-castle-ascot-legoland-free-parking-super-close/BC-10037753" class="class="static-page-link"">BEAUTIFUL WINDSOR COTTAGE, AMAZING LOCATION, The Castle, Ascot, Legoland, Free Parking Super Close</a> <a href="/property/grade-ii-listed-victorian-cottage/BC-12530419" class="class="static-page-link"">Grade II listed Victorian cottage</a> <a href="/property/weekly-and-monthly-stay-deals-heartwarming-windsor-cottage-with-free-parking-perfect-for-contractor/BC-10964400" class="class="static-page-link"">WEEKLY AND MONTHLY STAY DEALS - Heartwarming Windsor Cottage with Free Parking, Perfect for Contractor and Relocators Long Term Stays!</a> <a href="/property/stylish-3-bed-cottage-walk-2-all-sights-high-st/BC-7927636" class="class="static-page-link"">STYLISH 3 BED COTTAGE, WALK 2 ALL SIGHTS &amp; HIGH ST</a> <a href="/property/garfield-place-cosy-2-bedroom-cottage-central-windsor-with-parking/BC-1176183" class="class="static-page-link"">Garfield Place Cosy 2-Bedroom Cottage Central Windsor with Parking</a> <a href="/property/castle-properties-the-duchess-3-bed-family-cottage/BC-3036624" class="class="static-page-link"">Castle Properties: The Duchess, 3 Bed Family cottage</a> <a href="/property/charming-windsor-cottage-incredible-location-castle-doorstep/BC-11186238" class="class="static-page-link"">CHARMING WINDSOR COTTAGE, INCREDIBLE Location, Castle Doorstep</a> <a href="/property/charming-cottage-in-windsor-walk-to-castle-shops/BC-6520655" class="class="static-page-link"">Charming cottage in WINDSOR - WALK TO CASTLE &amp;SHOPS!</a> <a href="/property/inviting-2-bed-cottage-in-windsor/BC-9164860" class="class="static-page-link"">Inviting 2-Bed Cottage in Windsor</a> <a href="/property/chestnut-cottage-stunning-countryside-views-parking-4-bed-3-bathrooms/BC-6772504" class="class="static-page-link"">Chestnut Cottage - Stunning Countryside Views! PARKING, 4 BED, 3 BATHROOMS</a>

How much does it cost to rent a cottage in Windsor and Maidenhead?

The average cost for a cottage rental in Windsor and Maidenhead is $589 per night. Nighttravels has a wide list of great cottages near Windsor and Maidenhead that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windsor and Maidenhead that allow pets?

Yes, here are the top cottage rentals in Windsor and Maidenhead that allow you to bring your pet: Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle Charming 3BR Cottage Near Windsor and Sights Inviting 2-bed Cottage in Windsor THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE <a href="/all/united-kingdom/england/windsor-and-maidenhead" class="class="static-page-link"">See all pet-friendly vacation rentals in Windsor and Maidenhead on Nighttravels</a>

Do you have any rental cottages in Windsor and Maidenhead that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windsor and Maidenhead to find one that works for you.

Are there quality cottages in Windsor and Maidenhead that have indoor swimming pools?

As of 2026, the data from Nighttravels shows that there are Over 69 private swimming pools or cottages with indoor pools in the Windsor and Maidenhead area along with other great amenities.

Windsor and Maidenhead Cottage Rentals By Owner

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle

From US $437

10.0 (106 Reviews)

Cottage

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle

Parking
Pet Friendly
TV

Windsor and Maidenhead Cottage Rentals & Holiday Homes

Find the best cottages in Windsor and Maidenhead - We found 69 exact matches

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